DE2431582A1 - O-AMINOSULFONYL-GLYCOLIC ACID AMIDE - Google Patents
O-AMINOSULFONYL-GLYCOLIC ACID AMIDEInfo
- Publication number
- DE2431582A1 DE2431582A1 DE2431582A DE2431582A DE2431582A1 DE 2431582 A1 DE2431582 A1 DE 2431582A1 DE 2431582 A DE2431582 A DE 2431582A DE 2431582 A DE2431582 A DE 2431582A DE 2431582 A1 DE2431582 A1 DE 2431582A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- substituted
- glycolic acid
- diallylamide
- aminosulfonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- DEARLNUFMWSREQ-UHFFFAOYSA-N sulfamoyl 2-hydroxyacetate Chemical compound NS(=O)(=O)OC(=O)CO DEARLNUFMWSREQ-UHFFFAOYSA-N 0.000 title claims description 3
- -1 aminosulf o Chemical class 0.000 claims description 32
- 150000001408 amides Chemical class 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 235000021533 Beta vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 3
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 3
- 235000005781 Avena Nutrition 0.000 description 3
- 241000209761 Avena Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000011293 Brassica napus Nutrition 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 240000004296 Lolium perenne Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- BQKCJNGDDGMGEN-UHFFFAOYSA-N 1,3-dioxolane-2,4-dione Chemical compound O=C1COC(=O)O1 BQKCJNGDDGMGEN-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- 241000209764 Avena fatua Species 0.000 description 2
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- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219193 Brassicaceae Species 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000871189 Chenopodiaceae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000195952 Equisetaceae Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000209219 Hordeum Species 0.000 description 2
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- 241000219071 Malvaceae Species 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000013557 Plantaginaceae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000003337 fertilizer Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
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- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Unser Zeichen: O. Z. 30 637 H/AR 6700 Ludwigshafen, 28. 6. 1'974Our reference: O. Z. 30 637 H / AR 6700 Ludwigshafen, June 28, 1974
O-Aminosulfonyl-glykolsäureamideO-aminosulfonyl glycolic acid amides
Die vorliegende Erfindung betrifft neue, wertvolle substituierte Ο-/""AminosulfonylT-glykolsäureamide, ihre Herstellung, Herbizide, die diese Verbindungen enthalten, und ihre Verwendung als Herbizide.The present invention relates to new, valuable substituted Ο - / "" aminosulfonylT-glycolic acid amides, their production, herbicides, containing these compounds and their use as herbicides.
Es ist bekannt, N,N-Diallyl-2-chlor-acetamid als Herbizid zu verwenden, es ist jedoch nur wenig wirksam (D.A.S. 1 OH 380).It is known to use N, N-diallyl-2-chloro-acetamide as a herbicide use, but it is not very effective (D.A.S. 1 OH 380).
Ebenso ist bekannt, daß 0-(Isopropylaminosulfonyl)-glykolsäure-N-butin-1-yl-3-anilid (DOS 2 201 432) eine herbizide Wirkung hat.It is also known that 0- (isopropylaminosulfonyl) -glycolic acid-N-butyn-1-yl-3-anilide (DOS 2 201 432) has a herbicidal effect.
Es wurde nun gefunden, daß substituierte 0-/~Aminosulfonyl/-glykolsäureamide der allgemeinen FormelIt has now been found that substituted O- / ~ aminosulfonyl / -glycolic acid amides the general formula
< if<if
^N-CCH0OSF^ N-CCH 0 OSF
R28 2 S VR 2 8 2 SV
1 2
in der R und R einen Alkylrest, einen Alkenyl-, Alkinyl-, Halogenalkyl- oder Cycloalkyl-Rest bedeuten und R und R für
Wasserstoff, Alkyl, Cycloalkyl oder Halogenalkyl stehen, eine bessere herbizide Wirkung haben als die bekannten Wirkstoffe.1 2
in which R and R are an alkyl radical, an alkenyl, alkynyl, haloalkyl or cycloalkyl radical and R and R are hydrogen, alkyl, cycloalkyl or haloalkyl, have a better herbicidal effect than the known active ingredients.
12 ·■12 · ■
R und R können beispielsweise bedeuten: Methyl, Äthyl, Propyl, i-Propyl, Butyl, i-Butyl, sec-Butyl, tert-Butyl, Pentyl, Allyl, Butenyl, Pentenyl, Hexenyl, Propargyl, Butinyl, Pentinyl, Hexinyl, 2-Chloräthyl, Cyclopentyl, Cyclohexyl.R and R can mean, for example: methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, tert-butyl, pentyl, allyl, Butenyl, pentenyl, hexenyl, propargyl, butynyl, pentynyl, hexynyl, 2-chloroethyl, cyclopentyl, cyclohexyl.
R und R sind beispielsweise: Wasserstoff, Methyl, Äthyl, Propyl, i-Propyl, Butyl, i-Butyl, sec-Butyl, tert.-Butyl, Pentyl, 2-Methylbutyl-3, Pentyl-3, 2-MethyIpenty1-3, 3-Methylpentyl-4, Hexyl, Cyclopentyl, Cyclohexyl, 2-Chloräthyl, 2-Fluoräthyl.R and R are for example: hydrogen, methyl, ethyl, Propyl, i-propyl, butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 2-methylbutyl-3, pentyl-3, 2-methylpentyl-3, 3-methylpentyl-4, Hexyl, cyclopentyl, cyclohexyl, 2-chloroethyl, 2-fluoroethyl.
212/74 509884/1093 "2" 212/74 509884/1093 " 2 "
- 2 - υ.Ζ. 30 637- 2 - υ.Ζ. 30 637
24315922431592
Die neuen O-(Aminosulfonyl)-glykolsäureamide können entsprechend der folgenden allgemeinen Reaktionsgleichung aus einem G-lykolsäureamid und einem Aminosulfony!halogenid hergestellt werden:The new O- (aminosulfonyl) -glykolsäureamide can accordingly the following general reaction equation from a glycolic acid amide and an aminosulfonyl halide:
/R3 R1 P1 / R 3 R 1 P 1
N-C-CH0OH + ClSN -HCl. ^NCCHOSNC-CH 0 OH + ClSN -HCl. ^ NCCHOS
RO OR4 R O O R^RO OR 4 ROOR ^
wobei R , R , R und R die oben angegebene" Bedeutung haben. Diese Umsetzung wird vorzugsweise in Gegenwart eines säurebindenden Mittels, beispielsweise eines tertiären Amins wie Pyridin, Triäthylamin oder nach Zusatz wäßriger Lösungen einer anorganischen Base (Alkalihydroxide, Erda lka lihydr oxide), durchgeführt. where R, R, R and R have the meaning given above. This reaction is preferably carried out in the presence of an acid-binding agent, for example a tertiary amine such as Pyridine, triethylamine or, after the addition of aqueous solutions of an inorganic base (alkali hydroxides, Erda lka lihydr oxides), carried out.
Einer Lösung von 23,25 G-ewichtsteilen G-lykolsäure-N",M-diallylamid und 17,2 G-ewichtsteilen Triäthylamin in 100 G-ewichtsteilen Dichlormethan wurde unter Rühren bei O bis 50C eine Lösung von 24,4 G-ewichtsteilen Me thy la min ο sulf onylchlorid (ca. 90 gewichtsprozentig) in 40 G-ewichtsteilen Dichlormethan zudosiert.To a solution of 23.25 G-G-ewichtsteilen lykolsäure-N ', M-diallylamide and 17.2 G-ewichtsteilen triethylamine in 100 G-ewichtsteilen dichloromethane was added with stirring at O to 5 0 C a solution of 24.4 gsm parts by weight Me thy la min ο sulfonyl chloride (approx. 90% by weight) in 40 parts by weight of dichloromethane are added.
Zur Aufarbeitung wurde die Reaktionsmischung nacheinander mit Wasser, verdünnter Salzsäure, Wasser und verdünnter wäßriger Natriumbicarbonatlösung gewaschen. Die mit Magnesiumsulfat getrocknete organische Phase wurde im Vakuum eingeengt. Der Rückstand wurde aus Diäthyläther umkristallisiert: Pp. 47 C. Die Verbindung (0-(Methylaminosulfonyl)-glykolsäure-diallylamid) hat folgende Strukturformel:For work-up, the reaction mixture was successively mixed with water, dilute hydrochloric acid, water and dilute aqueous Washed sodium bicarbonate solution. The dried with magnesium sulfate organic phase was concentrated in vacuo. The residue was recrystallized from diethyl ether: pp. 47 C. Die Compound (0- (methylaminosulfonyl) -glycolic acid-diallylamide) has the following structural formula:
H2C=CH-CH2 OH 2 C = CH-CH 2 O
NN-C-CH2OS-NHCH3
H2C=CH-CH2 O O N NC-CH 2 OS-NHCH 3
H 2 C = CH-CH 2 OO
Auf entsprechendem Wege wurden die folgenden Verbindungen hergestellt:The following connections were established in the same way:
-3-50 9884/1093-3-50 9884/1093
- 3 - O. Z. 30 637- 3 - O. Z. 30 637
24315812431581
,1 0, 1 0
N-jf-CHg-Op-^
ΈΓ 0 OR' N-jf-CHg-Op- ^
ΈΓ 0 OR '
-4-50988A/1093 -4-50988A / 1093
R2 _ 4 -
R 2
2430.ζ. 30th
243
1582
°C7 bzw.657
1582
° C7 resp.
CH=C-CH(CH3 CH = C-CH (CH 3 )
CH = C-CH (CH 3
CH3 H
CH 3
HH
H
νΧΧ1?νΧΧ 1 ?
WXX *y WXX * y
509884/1093509884/1093
2431^82OZ 30 637 λα
2431 ^ 82
SeC-C4H9 C 4 H 9
SeC-C 4 H 9
CHjCHj
CHj
X-CjH7 C 3 H 7
X-CjH 7
HH
H
CHjCHj
CHj
HH
H
IV) IV)IV) IV)
UI UlUI ul
XXO ~~*O ^m \j XXi~iΤΤΓ1 - * / ™ ( fX DD
XXO ~~ * O ^ m \ j XXi ~ i
Die Herstellung der als Ausgangsstoffe einzusetzenden Glykolsäureamide kann in Anlehnung an das in J.Chem.Soc. 1357 (1951) beschriebene Verfahren durch Reaktion von 1,3-Dioxolan-2,4-dion mit geeigneten sekundären aliphatischen Aminen erfolgen, wie es in der folgenden Vorschrift erläutert wird.The production of the glycolic acid amides to be used as starting materials can be based on the in J.Chem.Soc. 1357 (1951) described process by reaction of 1,3-dioxolane-2,4-dione take place with suitable secondary aliphatic amines, as explained in the following procedure.
-6--6-
509884/1093509884/1093
- 6 - O.Z. 30 637- 6 - O.Z. 30 637
Einer Lösung von 150 Gewichtsteilen Diallylamin in 330 Gewichtsteilen Tetrahydrofuran wurde unter Rühren bei 20 bis 250C eine Lösung von 158 Gewichtsteilen 1,3-Dioxolan-2,4-dion in 230 Gewichtsteilen Tetrahydrofuran nach Maßgabe der Kohlendioxid-Entwicklung zudosiert. Nach dem Ende der Gasentwicklung wurde die Reaktionsmischung im Vakuum vom Lösungsmittel befreitA solution of 150 parts by weight of diallylamine in 330 parts by weight of tetrahydrofuran was metered in with stirring at 20 to 25 ° C., a solution of 158 parts by weight of 1,3-dioxolane-2,4-dione in 230 parts by weight of tetrahydrofuran in accordance with the evolution of carbon dioxide. After the evolution of gas had ceased, the reaction mixture was freed from the solvent in vacuo
und der Rückstand anschließend destilliert: Kpn ni __ 85°C, 2(- υ,υ ι mmand the residue is then distilled: Kp n ni __ 85 ° C, 2 (- υ, υ ι mm
idj. 1,4855. Die Verbindung Ν,Ν-Diallylglykolsäureamid hat folgende Strukturformel idj. 1.4855. The compound Ν, Ν-diallylglycolic acid amide has the following structural formula
HoC=CH-CHo
* ^N-C-CHoOHHoC = CH-CHo
* ^ NC-CHoOH
H2C=CH-CH2^ OH 2 C = CH-CH 2 ^ O
Ferner erhält man die als Ausgangsmaterialien erforderlichen Glykolsäureamide auf dem'durch die folgenden Gleichungen beschriebenen Weg:Furthermore, those required as starting materials are obtained Glycolic acid amides on the 'described by the following equations Path:
-HCl \R 1
-HCl \
O11
O
Tl 3
O 9 OCCH,
Tl 3
O
Il 2 Il
O O '"KF P * C ^ TT O C ^ P *" PT
Il 2 Il
OO
O y θ OCCH 3
O y
Π.Ο ν-Ό OXl,
^ Il J
O ■ τ nrtPTT
Π.Ο ν-Ό OXl,
^ Il J
O
Die dabei als Zwischenprodukte anfallenden Acetoxyacetamide lassen sich auch direkt herstellen, indem man Acetoxyacetylchlorid mit sekundären Aminen in Gegenwart eines Säureacceptors entsprechend der folgenden Reaktionsgleichung umsetzt:The acetoxyacetamides obtained as intermediate products can also be prepared directly by adding acetoxyacetyl chloride with secondary amines in the presence of an acid acceptor according to the following reaction equation:
^ + ClCCH2OCCH3 -HCl ? ^NC-CH2OCCH3 ^ + ClCCH 2 OCCH 3 -HCl ? ^ NC-CH 2 OCCH 3
R2 O . O R2 O OR 2 O. O R 2 OO
509884/1093509884/1093
- 7 - O.Z. JO 637- 7 - O.Z. JO 637
Die Anwendung der erfindungsgemäßen Verbindung» erfolgt z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen, auch hochprozentige ölige Suspensionen, oder Disper-r sionen, Emulsionen, Öldispersionen, Pasten Stäubemitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compound according to the invention is used e.g. in the form of directly sprayable solutions, powders, suspensions, also high-percentage oily suspensions, or dispersers sions, emulsions, oil dispersions, pastes, dusts, grit, granulates by spraying, atomizing, dusting, Scatter or pour. The forms of application depend entirely on the intended use; they should be in in each case ensure the finest possible distribution of the active ingredients according to the invention.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten und Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle usw., sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, zum Beispiel Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, z.B. Methanol, Äthanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron usw., stark polare Lösungsmittel, wie z.B. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser usw., in Betracht.Medium-sized mineral oil fractions are used for the production of directly sprayable solutions, emulsions, pastes and oil dispersions to a high boiling point, such as kerosene or diesel oil, furthermore coal tar oils etc., as well as oils of vegetable or animal origin Origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, e.g. methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, Isophorone, etc., strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc., into consideration.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern), Öldispersionen durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can consist of emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions can be prepared by adding water. The substances can be used to produce emulsions, pastes or oil dispersions as such or dissolved in an oil or solvent, homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers will. But it can also consist of active substances, wetting agents, adhesives, dispersants or emulsifiers and possibly Solvent or oil-based concentrates can be prepared, which are suitable for dilution with water.
An oberflächenaktiven Stoffen sind zu nennen: Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäuren, Phenolsulfonsäuren, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Alkali- und Erdalkalisalze der DibutyInaphthalin-The following surface-active substances should be mentioned: alkali, alkaline earth, Ammonium salts of lignosulphonic acid, naphthalenesulphonic acids, Phenol sulfonic acids, alkyl aryl sulfonates, alkyl sulfates, alkyl sulfonates, Alkali and alkaline earth salts of the dibutinaphthalene
-8--8th-
509884/1093509884/1093
- 8 - O.Z. "50 657- 8 - O.Z. "50 657
sulfonsäure, Lauryläthersulfat, Fettalkoholsulfate, fettsaure Alkali- und Erdalkalisalze, Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykoläther, Kondensationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyäthylen-octylphenolather, äthoxyliertes Isooctylphenol,- Octylphenol,- Nonylphenol, Alkylphenolpolyglykoläther, Tributylphenylpolyglykoläther, Alkylarylpolyätheralkohole, Isotridecylalkohol, Fettalkoholäthylenoxid-Kondensate, äthoxyliertes Rizinusöl, Polyoxyäthylenalkyläther, äthoxyliertes Polyoxypropylen, Laurylalkoholpolyglykolätheracetal, Sorbitester, Lignin, Sulfitablaugen und Methyllcellulose.sulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid Alkali and alkaline earth salts, salts of sulfated hexadecanols, Heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ethers, Condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, Ethoxylated isooctylphenol, - octylphenol, - nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, Alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, Sorbitol esters, lignin, sulphite waste liquors and methyll cellulose.
Pulver, Streu-und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powder, litter and dust can be mixed or mixed together Milling of the active substances with a solid carrier.
Granulate, z.B. TJmhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Talkum, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehle, Baumrinden-, HoIz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe. Granules, e.g. coated, impregnated and homogeneous granules, can by binding the active ingredients to solid carriers getting produced. Solid carriers are e.g. mineral earths such as silica gel, silicas, silica gels, silicates, Talc, kaolin, attaclay, limestone, lime, chalk, talc, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers, such as e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flours, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
Die Formulierungen enthalten zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gewichtsprozent.The formulations contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 percent by weight.
Zu den Mischungen oder Einzelwirkstoffen können öle verschiedenen Typs, Netz- oder Haftmittel, Herbizide, Fungizide, Nematozide, Insektizide, Bakterizide, Spurenelemente, Düngemittel, Antischaummittel (z.B. Silikone), Wachstumsregulatoren, Antidotmittel oder andere herbizid wirksame Verbindungen, wie z.B.In addition to the mixtures or individual active ingredients, oils can be different Type, wetting agents or adhesives, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, Antifoam agents (e.g. silicones), growth regulators, antidote agents or other herbicidally active compounds, such as e.g.
-9-50988Λ/1093 -9-50988Λ / 1093
- 9 - O.Z. 30- 9 - O.Z. 30th
substituierte Aniline, substituierte Aryloxycarbonsäuren sowie deren Salze, Ester und Amide, substituierte Äther, substituierte Arsonsäuren sowie deren Salze, Ester und Amide, substituierte Benzimidazole, substituierte Benzisothiazole, substituierte Benzthiadiazinondioxide, substituierte Benzoxazine, substituierte Benzoxazinone, substituierte Benzthiadiazole, substituierte Biursfce, substituierte Chinoline, substituierte Carbamate, substituierte aliphatische Carbonsäuren sowie deren Salze, Ester und Amide, substituierte aromatische Carbonsäuren sowie deren Salze, Ester und Amide, substituierte Carbamoylalkyl-thiol- oder -dithiophosphate, substituierte Chinazoline, substituierte Cycloalkylamidocarbonthiolsäuren sowie deren Salze, Ester und Amide, substituierte Cycloalkylcarbonamidothiazole, substituierte Dicarbonsäuren sowie Salze, Ester und Amide, substituierte Dihydrobenzofuranylsulfonate, substituierte Disulfide, substituierte Dipyridyliumsalze, substituierte Dithiocarbamate, substituierte Dithiophosphorsäuren sowie deren Salze, Ester und Amide, substituierte Harnstoffe, substituierte Hexahydro-1-H-carbothioate, substituierte Hydantoine, substituierte Hydrazide, substituierte Hydrazoniumsalze, substituierte Isooxaizolpyrimidone, substituierte Imidazole, substituierte Isothiazolpyrimidone, substituierte Ketone, substituierte Naphthochinone, substituierte aliphatische Nitrile, substituierte aromatische Nitrile, substituierte Oxadiazole, substituierte Oxadiazinone, substituierte Oxadiazolidindione, substituierte Oxadiazindione, substituierte Phenole sowie deren Salze und Ester, substituierte Phosphonsäuren sowie deren Salze, Ester und Amide, substituierte Phosphoniumchloride, substituierte Phosphonalkylglyzine, substituierte Phosphite, substituierte Phosphorsäuren sowie deren Salze, Ester und Amide, substituierte Piperidine, substituierte Pyrazole, substituierte Pyrazolelkylcarbonsäuren sowie deren Salze, Ester und Amide, substituierte Pyrazoliumsalze, substituierte Pyrazoliumalkylsulfate, substituierte Pyridazine, substituierte Pyridazone, substituierte Pyridincarbonsäuren sowie deren Salze, Ester und Amide, substituierte Pyridine, substituierte Pyridlncarboxylate, substituierte Pyridinone, substituierte Pyrimidine, substituierte Pyrimidone, substituierte Pyrrolidincarbonsäure sowie deren Salze, Ester undsubstituted anilines, substituted aryloxycarboxylic acids and their salts, esters and amides, substituted ethers, substituted Arsonic acids and their salts, esters and amides, substituted benzimidazoles, substituted benzisothiazoles, substituted Benzthiadiazinone dioxides, substituted benzoxazines, substituted benzoxazinones, substituted benzthiadiazoles, substituted Biursfce, substituted quinolines, substituted carbamates, substituted aliphatic carboxylic acids and their Salts, esters and amides, substituted aromatic carboxylic acids and their salts, esters and amides, substituted carbamoylalkyl-thiol or dithiophosphates, substituted quinazolines, substituted cycloalkylamidocarbon thiol acids and their Salts, esters and amides, substituted cycloalkylcarbonamidothiazoles, substituted dicarboxylic acids and salts, esters and Amides, substituted dihydrobenzofuranyl sulfonates, substituted Disulfide, substituted dipyridylium salts, substituted dithiocarbamates, substituted dithiophosphoric acids and their Salts, esters and amides, substituted ureas, substituted hexahydro-1-H-carbothioates, substituted hydantoins, substituted Hydrazides, substituted hydrazonium salts, substituted Isooxaizole pyrimidones, substituted imidazoles, substituted isothiazole pyrimidones, substituted ketones, substituted naphthoquinones, substituted aliphatic nitriles, substituted aromatic nitriles, substituted oxadiazoles, substituted oxadiazinones, substituted oxadiazolidinediones, substituted oxadiazinediones, substituted phenols and their salts and esters, substituted phosphonic acids and their salts, esters and amides, substituted phosphonium chlorides, substituted phosphonalkylglyzines, substituted Phosphites, substituted phosphoric acids and their salts, esters and amides, substituted piperidines, substituted Pyrazoles, substituted pyrazole alkyl carboxylic acids and their Salts, esters and amides, substituted pyrazolium salts, substituted pyrazolium alkyl sulfates, substituted pyridazines, substituted pyridazones, substituted pyridinecarboxylic acids and their salts, esters and amides, substituted pyridines, substituted pyridinecarboxylates, substituted pyridinones, substituted pyrimidines, substituted pyrimidones, substituted pyrrolidinecarboxylic acid and their salts, esters and
509884/1093 ~1°~509884/1093 ~ 1 ° ~
- 10 - 0.Z.50 637- 10 - 0.Z.50 637
Amide, substituierte Pyrrolidine, substituierte Pyrrolidone, substituierte Arylsulfonsäuren sowie deren Salze, Ester und Amide, substituierte Styrole, substituierte Tetrahydro-oxadiazindione, substituierte Tetrahydro-oxadiazoldione, substituierte Tetrahydromethanoindene, substituierte Tetrahydrodiazol-thione, substituierte Tetrahydro-thiadiazin-thione, substituierte Tetrahydro-thiadiazoldione, substituierte aromatische Thiocarbonsäureamide, substituierte Thiocarbonsäuren sowie deren Salze, Ester und Amide, substituierte Thiocarbamate, substituierte Thioharnstoffe, substituierte Thiophosphorsäuren sowie deren Salze, Ester und Amide, substituierte Triazine, substituierte Triazole, substituierte Uracile, substituierte Uretidindione, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix) zugesetzt werden. Die zuletzt genannten herbiziden Verbindungen können auch vor oder nach den erfindungsgemäßen Einzelwirkstoffen oder Mischungen zur Anwendung gebracht werden.Amides, substituted pyrrolidines, substituted pyrrolidones, substituted arylsulfonic acids and their salts, esters and Amides, substituted styrenes, substituted tetrahydro-oxadiazinediones, substituted tetrahydro-oxadiazole-diones, substituted tetrahydromethanoindenes, substituted tetrahydrodiazole-thiones, substituted tetrahydro-thiadiazine-thiones, substituted tetrahydro-thiadiazole-diones, substituted aromatic Thiocarboxamides, substituted thiocarboxylic acids and their salts, esters and amides, substituted thiocarbamates, substituted thioureas, substituted thiophosphoric acids and their salts, esters and amides, substituted triazines, substituted triazoles, substituted uracils, substituted uretidinediones, optionally also immediately before the Application (tank mix) can be added. The last-mentioned herbicidal compounds can also be used before or after the invention Individual active ingredients or mixtures can be used.
Die Zumischung dieser Mittel zu den erfindungsgemäßen Herbiziden kann im Gewichtsverhältnis 1:10 bis 10 : 1 erfolgen. Das Gleiche gilt für Öle, Fungizide, Nematozide, Insektizide, Bakterizide, Antidotmittel und Wachstumsregulatoren.The admixture of these agents to the herbicides according to the invention can be done in a weight ratio of 1:10 to 10: 1. The same goes for oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.
Die erfindungsgemäßen Mittel können u.a. im Vorpflanzverfahren, Nachpflanzverfahren, Vorsaatverfahren, Vorauflaufverfahren, Nachauflaufverfahren oder während des Auflaufens der Kulturpflanzen oder der unerwünschten Pflanzen ein- oder mehrmals angewandt werden.The agents according to the invention can inter alia in the preplanting process, Post-planting procedures, pre-sowing procedures, pre-emergence procedures, Post-emergence method or during emergence of the crop plants or the undesired plants one or more times can be applied.
Die Mittel weisen einen starken herbiziden Effekt auf und können deshalb als Unkrautvernichtungsmittel bzw. zur Bekämpfung unerwünschten Pflanzenwuches verwendet werden. Ob die Mittel als totale oder selektive Mittel wirken, hängt hauptsächlich von der Wirkstoffmenge je Flächeneinheit ab.The compositions have a strong herbicidal effect and can therefore be used as weed killers or for control unwanted vegetation can be used. Whether the means act as total or selective means mainly depends on the amount of active ingredient per unit area.
Unter Unkräutern bzw. unerwünschtem Pflanzenwuchs sind alle monokotylen und dikotylen Pflanzen zu verstehen, die an Orten aufwachsen, wo sie nicht erwünscht sind.All are under weeds or unwanted vegetation To understand monocotyledonous and dicotyledonous plants that grow in places where they are not wanted.
-11-509884/1093 -11-509884 / 1093
- 11 - 0.Z-. 30 6JT- 11 - 0.Z-. 30 6JT
So können mit den erfindungsgemäßen Mitteln beispielsweise Gramineen, wieFor example, Gramineae, such as
Cynodon spp. Dactylis spp.Cynodon spp. Dactylis spp.
Digitaria spp. Avena spp.Digitaria spp. Avena spp.
Echinochloa spp. Bromus spp.Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.Setaria spp. Uniola spp.
Panicum spp. Poa spp.Panicum spp. Poa spp.
Alopecurus spp. Leptochloa spp.Alopecurus spp. Leptochloa spp.
Lolium spp. Bracharia spp.Lolium spp. Bracharia spp.
Sorghum spp. Eleusine spp.Sorghum spp. Eleusine spp.
Agropyron spp. Cenchrus spp.Agropyron spp. Cenchrus spp.
Phalaris spp. Eragrostis spp.Phalaris spp. Eragrostis spp.
Apera spp. Phragmites communisApera spp. Phragmites communis
und andere
Cyperaceae, wieand other
Cyperaceae, like
Carex spp. Eleocharis spp.Carex spp. Eleocharis spp.
Cyperus spp. Scirpus spp.Cyperus spp. Scirpus spp.
und andereand other
dikotyle Unkräuter, wie Malvaceae, z.B.dicot weeds such as Malvaceae e.g.
Abutilon theoprasti Hibiscus spp.Abutilon theoprasti Hibiscus spp.
Sida spp. Malva spp. und andereSida spp. Malva spp. and other
Compostiae, wieCompostiae, like
Ambrosia spp. Gentaurea spp.Ambrosia spp. Gentaurea spp.
Lactuca spp. Tussilago spp.Lactuca spp. Tussilago spp.
Senecio spp. Lapsana communisSenecio spp. Lapsana communis
Sonchus spp. Tagetes spp.Sonchus spp. Tagetes spp.
Xanthium spp. Erigeron spp.Xanthium spp. Erigeron spp.
Iva spp. Anthemis spp.Iva spp. Anthemis spp.
Galinsoga spp. Matricaria spp.Galinsoga spp. Matricaria spp.
Taraxacum spp. Artemisia spp.Taraxacum spp. Artemisia spp.
Chrysanthemum spp. Bidens spp.Chrysanthemum spp. Bidens spp.
Cirsium spp. und andereCirsium spp. and other
-12· 50988Λ/ 1093-12 · 50988Λ / 1093
Convolvulaceae, wieConvolvulaceae, like
Convolvulus spp. Ipomoea spp. und andere O.Z. 30Convolvulus spp. Ipomoea spp. and other O.Z. 30th
Cuscuta spp. JacLuemontia tamnifoliaCuscuta spp. JacLuemontia tamnifolia
Cruciferae, wieCruciferae, like
Barbarea vulgaris Brassica spp. Capsella spp. Sisymbrium spp. TIiIaspi spp. Sinapis arvensis und andere Arabidopsis thaliana Descurainia spp. Draba spp. Coronopus didymus Lepidium spp. Raphanus spp.Barbarea vulgaris Brassica spp. Capsella spp. Sisymbrium spp. TIiIaspi spp. Sinapis arvensis and others Arabidopsis thaliana Descurainia spp. Draba spp. Coronopus didymus Lepidium spp. Raphanus spp.
G-eraniaceae, wieG-eraniaceae, like
Erodium spp. und andere Geranium spp.Erodium spp. and other Geranium spp.
Portulacaceae, wiePortulacaceae, like
Portulaca spp.Portulaca spp.
und andereand other
Primulaceae, wiePrimulaceae, like
Anagallis arvensis und andere lysimachiaAnagallis arvensis and other lysimachia
Rubiaceae, wieRubiaceae, like
Richardia spp, G-alium spp.Richardia spp, G-alium spp.
Diodia spp. und andereDiodia spp. and other
Scrophulariaceae, wie linaria spp. Veronica spp.Scrophulariaceae such as linaria spp. Veronica spp.
Digitalis spp. und andereDigitalis spp. and other
Solanaceae, wieSolanaceae, like
Physalis spp. Solanum spp. und andere Mcandra spp. Datura spp.Physalis spp. Solanum spp. and other Mcandra spp. Datura spp.
509884/ 1 093509884/1 093
-13--13-
Urticaceae, wieUrticaceae, like
TJrtica spp.TJrtica spp.
O.Z. 50O.Z. 50
Violaceae, wieViolaceae, like
Viola spp.Viola spp.
und andereand other
Zygophyllaceae, wieZygophyllaceae, such as
Tribulus terrestis und andereTribulus terrestis and others
Euphorbiaceae, wieEuphorbiaceae, like
Mercurialis annua Euphorbia spp,Mercurialis annua Euphorbia spp,
Umbelliferae, wieUmbelliferae, like
Daucus carota Aethusa cynapium Ammi ma jus und andereDaucus carota Aethusa cynapium Ammi ma jus and others
CommelinaeaeCommelinaeae
Commelina spp, und andereCommelina spp, and others
Labiatae, wieLabiatae, like
Lamium spp. und andere Galeopsis spp.Lamium spp. and other Galeopsis spp.
Leguminosae, wieLeguminosae, like
Medicago spp. Trifolium spp. Vicia spp. und andere Sesbania exaltata Cassia spp. Lathyrus spp.Medicago spp. Trifolium spp. Vicia spp. and other Sesbania exaltata Cassia spp. Lathyrus spp.
Plantaginaceae, wiePlantaginaceae, such as
Plantago spp, und anderePlantago spp, and others
Polygonaceae, wiePolygonaceae, like
Polygonum spp, Rumex spp.Polygonum spp, Rumex spp.
Pagopyrum spp, und anderePagopyrum spp, and others
Aizoaceae, wieAizoaceae, like
Molluga verticillata und andereMolluga verticillata and others
509884/1093509884/1093
-14--14-
H-H-
O. Z.O. Z.
Amaranthaceae, wieAmaranthaceae, like
Amaranthus spp.Amaranthus spp.
und andereand other
Boraginaceae, wieBoraginaceae, like
Amsinckia spp. Myostis spp. und andere Anchusa spp. LithospermumAmsinckia spp. Myostis spp. and other Anchusa spp. Lithospermum
Caryophyllaceae, wieCaryophyllaceae, such as
Stellaria spp. Spergula spp. Saponaria spp. Scleranthus annuus Silene spp. Gerastium spp. Agrostemma githago und andereStellaria spp. Spergula spp. Saponaria spp. Scleranthus annuus Silene spp. Gerastium spp. Agrostemma pallida and other
Chenopodiaceae, wieChenopodiaceae, such as
Ciienopodium spp. Kochia spp. Sa Is ο la EaIi Atriplex spp. Monolepsis nuttalliana und andereCiienopodium spp. Kochia spp. Sa Is ο la EaIi Atriplex spp. Monolepsis nuttalliana and other
Lythraceae, wieLythraceae, like
Cuphea spp, und andereCuphea spp, and others
Oxalidaceae, wieOxalidaceae, such as
Oxalis spp,Oxalis spp,
RanunculaGeae, wieRanunculaGeae, like
Ranunculus spp, Delphinium spp, Adonis spp. und andereRanunculus spp, Delphinium spp, Adonis spp. and other
Papaveraceae, wiePapaveraceae, like
Papaver spp. und andere Pumaria officinalisPapaver spp. and others Pumaria officinalis
Onagraceae, wieOnagraceae, like
Jussiaea spp.Jussiaea spp.
und andereand other
Ro saceae, wieRo saceae, like
Alchemillia spp. und andere Potentilla spp,Alchemillia spp. and other Potentilla spp,
-15--15-
509884/1093509884/1093
Potamögetonaceae, wiePotamögetonaceae, such as
Potamogeton spp.Potamogeton spp.
O.ZOOO.ZOO
und andereand other
Najadaceae, wieNajadaceae, like
Najas «pp.Najas «pp.
und andereand other
Marsilea, wieMarsilea how
Marsilea quadrifoliaMarsilea quadrifolia
und andereand other
Polypodiaceae, wiePolypodiaceae such as
Pteridium aguilinumPteridium aguilinum
Alismataceae, wieAlismataceae, such as
Alisma spp. und andereAlisma spp. and other
Sagittaria sagittifoliaSagittaria sagittifolia
Equisetaceae, wieEquisetaceae, such as
Equisetaceae spp.Equisetaceae spp.
und andereand other
bekämpft werden.be fought.
Die erfindungsgemäßen Mittel können in ihrer aufgewandten Menge schwanken. Die aufgewandte Menge hängt hauptsächlich von der Art des gewünschten Effekts ab.The agents according to the invention can be used in the amount used vary. The amount used depends mainly on the type of effect desired.
Die Aufwandmenge liegt im allgemeinen zwischen 0,1 und 15 oder mehr, vorzugsweise 0,2 und 6 kg Wirkstoff pro Hektar.The application rate is generally between 0.1 and 15 or more, preferably 0.2 and 6 kg of active ingredient per hectare.
Die erfindungsgemäßen Mittel können in Getreidekulturen, wieThe agents according to the invention can be used in cereal crops, such as
Avena spp. Triticum spp. Hordeum spp. Seeale spp. Saccharum officinarumAvena spp. Triticum spp. Hordeum spp. Seeale spp. Saccharum officinarum
Sorghum
Zea maysSorghum
Zea mays
Panicum miliaceum Oryza spp.Panicum miliaceum Oryza spp.
und in Kulturen von Dikotyledonen, wie Cruciferae, z.B.and in cultures of dicotyledons such as Cruciferae, e.g.
-16--16-
50988Λ/109350988Λ / 1093
Brassica spp. Sinapis spp. Raphanus spp. Lepidium spp.Brassica spp. Sinapis spp. Raphanus spp. Lepidium spp.
O.Z.50O.Z. 50
Composistae, z.B.Composistae, e.g.
Lactuca spp. Helianthus spp. Gartnamus spp. Scorzonera spp.Lactuca spp. Helianthus spp. Gartnamus spp. Scorzonera spp.
Malvaceae, z.B.Malvaceae, e.g.
Grossypium hirsutumGrossypium hirsutum
Leguminosae, z.B.Leguminosae, e.g.
Medicago spp. Trifolium spp. Pisum spp. Phaseolus spp. Arachis spp. G-lye ine maxMedicago spp. Trifolium spp. Pisum spp. Phaseolus spp. Arachis spp. G-lye ine max
Chenopodiaceae, z.B. Beta spp. Spinacia spp.Chenopodiaceae, e.g. Beta spp. Spinacia spp.
Solanaceae, z.B.Solanaceae e.g.
Solanum spp. Nicotiania spp. Capsicum annuumSolanum spp. Nicotiania spp. Capsicum annuum
Linaceae, z.B.Linaceae, e.g.
Linum spp,Linum spp,
IMbelliferae, z.B.IMbelliferae, e.g.
Petroselinum spp. Baucus carota Apium graveolensPetroselinum spp. Baucus carota Apium graveolens
Rosaceae, z.B.Rosaceae, e.g.
FragariaFragaria
Cucurbitaceae, z.B.Cucurbitaceae, e.g.
Cucumis spp, Cucurbita spp,Cucumis spp, Cucurbita spp,
Liliaceae, z.B.Liliaceae, e.g.
Allium spp.Allium spp.
509884/10 93509884/10 93
Vitaceae, z.B.Vitaceae, e.g.
Vitis viniferaVitis vinifera
Bromeliaceae, z.B.Bromeliaceae e.g.
Ananas sativusPineapple sativus
angewandt werden.can be applied.
- 17 - O.ZOO 637- 17 - O.ZOO 637
Im Gewächshaus wurde lehmiger Sandboden in Versuchsgefäße gefüllt und mit Samen verschiedener Pflanzen "besät.In the greenhouse, loamy sandy soil was filled into test pots and "sown" with seeds from various plants.
Unmittelbar danach erfolgte die Behandlung mitImmediately thereafter, the treatment was carried out with
I O-(Isopropylaminosulfonyl)-glykolsäure-N,N-diallylamidI O- (Isopropylaminosulfonyl) -glycolic acid-N, N-diallylamide
II 0-(Äthylamino sulfonyl)-glykolsäure-N,N-diallylamidII 0- (ethylamino sulfonyl) -glycolic acid-N, N-diallylamide
III 0-(Propylaminosulfonyl)-glykolsäure-N,li-diallylamidIII 0- (propylaminosulfonyl) -glycolic acid-N, li-diallylamide
IV 0-(Butylaminosulfonyl)-glykolsäure-N,N-diallylamidIV 0- (Butylaminosulfonyl) -glycolic acid-N, N-diallylamide
V 0-(sec-Butylaminosulfonyl)-glykolsäure-N,N-diallylamidV 0- (sec-butylaminosulfonyl) -glycolic acid-N, N-diallylamide
VI 0-(Methylaminosulfonyl)-glykolsäure-N,N-diallylamid undVI 0- (methylaminosulfonyl) -glycolic acid-N, N-diallylamide and
VII N,N-Diallyl-2-chloracetamidVII N, N-diallyl-2-chloroacetamide
IX 0-(i-Propy laminosulf onyl)-glykolsäure-li-butin-1-y 1-3-IX 0- (i-Propy laminosulfonyl) -glycolic acid-li-butyne-1-y 1-3-
anilid
als Vergleichswirkstoffe.anilide
as comparative active ingredients.
Die Aufwandmenge betrug jeweils 3 kg Aktivsubstanz pro Hektar und war jeweils in 500 Liter Wasser je Hektar dispergiert oder emulgiert.The application rate was 3 kg of active ingredient per hectare and was in each case dispersed in 500 liters of water per hectare or emulsified.
Nach 4 bis 5 Wochen wurde festgestellt, daß die Wirkstoffe I bis VI eine bessere Verträglichkeit gegenüber den Kulturpflanzen Brassica napus und Beta vulgaris als die Verbindung IX und eine bessere herbizide Wirkung als der Wirkstoff VIII zeigten.After 4 to 5 weeks it was found that the active ingredients I to VI better tolerance to the cultivated plants Brassica napus and Beta vulgaris than the compound IX and a better herbicidal effect than the active ingredient VIII showed.
Das Versuchsergebnis ist auch nachfolgender Tabelle zu ersehen:The test result can also be seen in the following table:
-18-509884/1093 -18-509884 / 1093
kg/haActive ingredient
kg / ha
71Γ1582
71Γ
VI243
VI
galli 1Echinochloa crus
galli 1
0 = ohne Schädigung
100 = totale Schädigung0 = without damage
100 = total damage
Im Gewächshaus wurden verschiedene Pflanzen bei einer Wuchshöhe von 8 bis 16 cm mit den Wirkstoffen I bis VII und mit VIII (0-(2-Chloräthylaminosulfonyl)-glykolsäure-N,E-diallylamid) behandelt.In the greenhouse, various plants at a height of 8 to 16 cm with the active ingredients I to VII and with VIII (0- (2-chloroethylaminosulfonyl) -glycolic acid-N, E-diallylamide) treated.
Die Aufwandmenge betrug jeweils 3 kg Aktivsubstanz pro Hektar und war jeweils in 500 Liter Wasser je Hektar dispergiert oder emulgiert.The application rate was 3 kg of active ingredient per hectare and was in each case dispersed in 500 liters of water per hectare or emulsified.
Nach 2 bis 3 Wochen wurde festgestellt, daß die Wirkstoffe I bis VI und der Wirkstoff VIII eine bessere Verträglichkeit gegenüber den Kulturpflanzen und eine bessere herbizide Wirkung zeigten als der Wirkstoff VII.After 2 to 3 weeks it was found that the active ingredients I to VI and the active ingredient VIII a better tolerance towards the crop plants and a better herbicidal action showed as the active ingredient VII.
Das Versuchsergebnis ist auch nachfolgender Tabelle zu ersehen: The test result can also be seen in the following table:
-19-50988A/ 1 093-19-50988A / 1 093
kg/haActive ingredient
kg / ha
VII VIII2431582
VII VIII
galliEchinochloa crus
galli
0 = ohne Schädigung
100 = totale Schädigung0 = without damage
100 = total damage
Im Gewächshaus wurde lehmiger Sandboden in Versuchgefäße gefüllt und mit verschiedenen Samen "besät. Unmittelbar danach erfolgte die Behandlung mit 0-(2-Chloräthylaminosulfonyl)-glykolsäure-N,N-diallylamid (VIII) im Vergleich mit N,N-Diallyl-chloracetamid (VII). Die Aufwandmenge "betrug jeweils 2 kg Aktivsubstanz pro Hektar und war jeweils in 500 Liter Wasser je Hektar dispergiert oder emulgiert.In the greenhouse, loamy sandy soil was filled into test vessels and sown with various seeds. Immediately thereafter, the treatment with 0- (2-chloroethylaminosulfonyl) -glycolic acid-N, N-diallylamide took place (VIII) in comparison with N, N-diallyl-chloroacetamide (VII). The application rate "was 2 kg of active substance in each case per hectare and was in each case dispersed or emulsified in 500 liters of water per hectare.
Nach vier bis fünf Wochen wurde festgestellt, daß der Wirkstoff VIII eine bessere Verträglichkeit an den Kulturpflanzen und eine bessere herbizide Wirkung zeigte als der Wirkstoff VII.After four to five weeks it was found that the active ingredient VIII is better tolerated by the crop plants and showed a better herbicidal effect than active ingredient VII.
Das Versuchsergebnis ist aus'' nachfolgender Tabelle zu ersehen:The test result can be seen from '' the table below:
kg/haActive ingredient
kg / ha
2VIII
2
2VII
2
50988Λ/ 109310
50988Λ / 1093
Man vermischt 90 Gewichtsteile der Verbindung I mit 10 Gewicht steilen F-Methyl-t-pyrrolidon und erhält eine lösung, die zur Anwendung in Form kleinster Tropfen geeignet ist.90 parts by weight of compound I are mixed with 10 parts by weight of F-methyl-t-pyrrolidone and a solution is obtained which is suitable for use in the form of tiny drops.
20 Gewichtsteile der Verbindung II werden in einer Mischung gelöst, die aus 80 Gewichtsteilen Xylol, 10 Gewichtsteilen des Anlagerungsprodukteβ von 8 bis 10 Mol Äthylenoxid an 1 Mol Ölsäure-N-monoäthanolamid, 5 Gewichtsteilen Calciumsalz der Dodeeylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.20 parts by weight of compound II are dissolved in a mixture consisting of 80 parts by weight of xylene and 10 parts by weight of the addition products of 8 to 10 mol of ethylene oxide with 1 Mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct consists of 40 moles of ethylene oxide in 1 mole of castor oil. By pouring out and finely distributing the solution in 100,000 parts by weight of water give an aqueous dispersion which contains 0.02 percent by weight of the active ingredient.
20 Gewichtsteile der Verbindung III werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsprodukts von 7 Mol Äthylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Eicinusöl besteht. Durch Eingießen und feines Verteilen der lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.20 parts by weight of the compound III are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 Moles of eicinus oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives a aqueous dispersion containing 0.02 percent by weight of the active ingredient.
509884/1093509884/1093
- 21 - O.Z. 50 637- 21 - O.Z. 50 637
: Beispiel'8 : Example'8
20 Gewichtsteile der Verbindung IV werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanol, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 2800C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält,20 parts by weight of the compound IV are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02 percent by weight of the active ingredient.
. . : ■■-... ^Beispiel 9 . . ■■_,·. . · ■ ■. . : ■■ -... ^ Example 9. . ■■ _, ·. . · ■ ■
20 Gewichtsteile des Wirkstoffs VI werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnäphthalin-^-sulfonsäure, 17 Gewichtsteilen des Natriumsalzes .einer Ligninsulfonsäure aus einer SuIfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20 000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gewichtsprozent des Wirkstoffs enthält, 20 parts by weight of the active ingredient VI are 3 parts by weight of the sodium salt of diisobutylnäphthalin - ^ - sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a SuIfit waste liquor and 60 parts by weight of powdered Silica gel mixed well and ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which contains 0.1 percent by weight of the active ingredient.
3 Gewichtsteile der Verbindung I werden mit 97 Gewichtsteilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gewichtsprozent des Wirkstoffs enthält.3 parts by weight of compound I are intimately mixed with 97 parts by weight of finely divided kaolin. One receives on this Way a dust that contains 3 percent by weight of the active ingredient.
30 Gewichtsteile der Verbindung II werden mit einer Mischung aus 92 Gewichtsteilen pulverförmigem Kieselsäuregel und 8 Gewichtsteilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit. 30 parts by weight of compound II are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil, which has been sprayed onto the surface of this silica gel, is intimately mixed. One receives on this way a preparation of the active ingredient with good adhesion.
5 0 9 8 8 4/109 35 0 9 8 8 4/109 3
Claims (15)
in der R und R die oben genannten Bedeutungen haben, mit einem Aminosulfonylhalogenid der Formel12th
in which R and R have the meanings given above, with an aminosulfonyl halide of the formula
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2431582A DE2431582A1 (en) | 1974-07-01 | 1974-07-01 | O-AMINOSULFONYL-GLYCOLIC ACID AMIDE |
| BG030259A BG26507A3 (en) | 1974-07-01 | 1975-06-11 | HERBICIDE |
| JP50070975A JPS519721A (en) | 1974-07-01 | 1975-06-13 | |
| US05/587,355 US4009192A (en) | 1974-07-01 | 1975-06-16 | O-aminosulfonylglycolic amides |
| IT50176/75A IT1040685B (en) | 1974-07-01 | 1975-06-23 | HERBICIDE |
| BE157739A BE830704A (en) | 1974-07-01 | 1975-06-26 | O- (AMINOSULFUNYL) -GLYCOLIC AMIDES |
| BR5161/75D BR7504016A (en) | 1974-07-01 | 1975-06-26 | HERBICIDAL COMPOSITES |
| DD186939A DD118366A5 (en) | 1974-07-01 | 1975-06-27 | |
| YU01652/75A YU165275A (en) | 1974-07-01 | 1975-06-27 | Process for the synthesis of herbicidal o-amino-sulfonyl glycolic acid amides |
| SU752150211A SU651644A3 (en) | 1974-07-01 | 1975-06-30 | Herbicide |
| AT501075A AT342365B (en) | 1974-07-01 | 1975-06-30 | HERBICIDE |
| PL1975181662A PL96585B1 (en) | 1974-07-01 | 1975-06-30 | A WORMHOUSE |
| ES438985A ES438985A1 (en) | 1974-07-01 | 1975-06-30 | O-aminosulfonylglycolic amides |
| CA230,431A CA1043804A (en) | 1974-07-01 | 1975-06-30 | O-aminosulfonylglycolic amides |
| ZA00754161A ZA754161B (en) | 1974-07-01 | 1975-06-30 | O-(aminosulfonyl)-glycolic amides |
| FR7520490A FR2277079A1 (en) | 1974-07-01 | 1975-06-30 | O- (AMINOSULFONYL) GLYCOLIC ACID AMIDES USEFUL AS HERBICIDAL AGENTS |
| CH847775A CH609207A5 (en) | 1974-07-01 | 1975-06-30 | |
| AR259415A AR213614A1 (en) | 1974-07-01 | 1975-06-30 | NEW O- (AMINOSULFONIL) -GLYCOLILAMIDE DERIVATIVES AND HERBICIDAL COMPOSITIONS CONTAINING THEM |
| GB27463/75A GB1502798A (en) | 1974-07-01 | 1975-06-30 | O-aminosulphonylglycolic amides |
| HU75BA00003296A HU172118B (en) | 1974-07-01 | 1975-06-30 | Herbicide compositions containing amides of o-bracket-aminosulphonyl-bracket closed-glycolic acid, and process for producing the active agents |
| EG374/75A EG11751A (en) | 1974-07-01 | 1975-06-30 | Process for the production of herbicidally-o-aminosulfonyl-glycolic amides used as herbicides |
| NL7507763A NL7507763A (en) | 1974-07-01 | 1975-06-30 | PROCESS FOR THE PREPARATION OF HERBICIDE ACTIVE GLY COLIC ACID AMIDES, PROCESS FOR THE PREPARATION OF HERBICIDE ACTIVE PREPARATIONS AND FORMED PREPARATIONS. |
| CS754669A CS197249B2 (en) | 1974-07-01 | 1975-07-01 | Herbicide means |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2431582A DE2431582A1 (en) | 1974-07-01 | 1974-07-01 | O-AMINOSULFONYL-GLYCOLIC ACID AMIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2431582A1 true DE2431582A1 (en) | 1976-01-22 |
Family
ID=5919422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2431582A Withdrawn DE2431582A1 (en) | 1974-07-01 | 1974-07-01 | O-AMINOSULFONYL-GLYCOLIC ACID AMIDE |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4009192A (en) |
| JP (1) | JPS519721A (en) |
| AR (1) | AR213614A1 (en) |
| AT (1) | AT342365B (en) |
| BE (1) | BE830704A (en) |
| BG (1) | BG26507A3 (en) |
| BR (1) | BR7504016A (en) |
| CA (1) | CA1043804A (en) |
| CH (1) | CH609207A5 (en) |
| CS (1) | CS197249B2 (en) |
| DD (1) | DD118366A5 (en) |
| DE (1) | DE2431582A1 (en) |
| EG (1) | EG11751A (en) |
| ES (1) | ES438985A1 (en) |
| FR (1) | FR2277079A1 (en) |
| GB (1) | GB1502798A (en) |
| HU (1) | HU172118B (en) |
| IT (1) | IT1040685B (en) |
| NL (1) | NL7507763A (en) |
| PL (1) | PL96585B1 (en) |
| SU (1) | SU651644A3 (en) |
| YU (1) | YU165275A (en) |
| ZA (1) | ZA754161B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123255A (en) * | 1977-01-03 | 1978-10-31 | Chevron Research Company | O-sulfonyl-alpha-cyano 2,6-dihalobenzaldoximes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536721A (en) * | 1963-09-13 | 1970-10-27 | Stauffer Chemical Co | Substituted-sulfonyl glycolamide compositions |
| BE792364A (en) * | 1971-12-06 | 1973-06-06 | Basf Ag | SUBSTITUTION DERIVATIVES OF SULFONYLGLYCOLANILIDE |
| BE794013A (en) * | 1972-01-13 | 1973-07-12 | Basf Ag | O- (AMINOSULFONYL) -GLYCOLIC ACID ANILIDES SUBSTITUTES |
-
1974
- 1974-07-01 DE DE2431582A patent/DE2431582A1/en not_active Withdrawn
-
1975
- 1975-06-11 BG BG030259A patent/BG26507A3/en unknown
- 1975-06-13 JP JP50070975A patent/JPS519721A/ja active Pending
- 1975-06-16 US US05/587,355 patent/US4009192A/en not_active Expired - Lifetime
- 1975-06-23 IT IT50176/75A patent/IT1040685B/en active
- 1975-06-26 BR BR5161/75D patent/BR7504016A/en unknown
- 1975-06-26 BE BE157739A patent/BE830704A/en unknown
- 1975-06-27 DD DD186939A patent/DD118366A5/xx unknown
- 1975-06-27 YU YU01652/75A patent/YU165275A/en unknown
- 1975-06-30 PL PL1975181662A patent/PL96585B1/en unknown
- 1975-06-30 HU HU75BA00003296A patent/HU172118B/en unknown
- 1975-06-30 AT AT501075A patent/AT342365B/en not_active IP Right Cessation
- 1975-06-30 AR AR259415A patent/AR213614A1/en active
- 1975-06-30 ZA ZA00754161A patent/ZA754161B/en unknown
- 1975-06-30 SU SU752150211A patent/SU651644A3/en active
- 1975-06-30 GB GB27463/75A patent/GB1502798A/en not_active Expired
- 1975-06-30 CA CA230,431A patent/CA1043804A/en not_active Expired
- 1975-06-30 EG EG374/75A patent/EG11751A/en active
- 1975-06-30 ES ES438985A patent/ES438985A1/en not_active Expired
- 1975-06-30 CH CH847775A patent/CH609207A5/xx not_active IP Right Cessation
- 1975-06-30 NL NL7507763A patent/NL7507763A/en not_active Application Discontinuation
- 1975-06-30 FR FR7520490A patent/FR2277079A1/en active Granted
- 1975-07-01 CS CS754669A patent/CS197249B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2277079B1 (en) | 1978-07-28 |
| BR7504016A (en) | 1976-06-29 |
| CH609207A5 (en) | 1979-02-28 |
| HU172118B (en) | 1978-06-28 |
| YU165275A (en) | 1982-02-28 |
| ES438985A1 (en) | 1977-02-16 |
| ZA754161B (en) | 1976-06-30 |
| ATA501075A (en) | 1977-07-15 |
| JPS519721A (en) | 1976-01-26 |
| SU651644A3 (en) | 1979-03-05 |
| BE830704A (en) | 1975-12-29 |
| NL7507763A (en) | 1976-01-05 |
| CS197249B2 (en) | 1980-04-30 |
| BG26507A3 (en) | 1979-04-12 |
| DD118366A5 (en) | 1976-03-05 |
| GB1502798A (en) | 1978-03-01 |
| PL96585B1 (en) | 1978-01-31 |
| AT342365B (en) | 1978-03-28 |
| US4009192A (en) | 1977-02-22 |
| AR213614A1 (en) | 1979-02-28 |
| IT1040685B (en) | 1979-12-20 |
| CA1043804A (en) | 1978-12-05 |
| FR2277079A1 (en) | 1976-01-30 |
| EG11751A (en) | 1979-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |